9 Things To Do in Chicago This Labor Day Weekend 2025
CHICAGO, Illinois — Labor Day weekend is the unofficial end of summer, but Chicago keeps the celebrations alive with festivals, concerts, cultural events, and outdoor activities. From house music in Union Park to biking Lake Shore Drive, here are nine ways to make the most of your long weekend.
1. Bike the Drive
One of the city’s most unique traditions, Bike the Drive closes DuSable Lake Shore Drive to cars, opening it exclusively for cyclists. Riders can enjoy sweeping lakefront views in a car-free environment while supporting the Active Transportation Alliance.
- When/Where: Sunday, Aug. 31, 6 a.m.–12 p.m., Butler Field in Grant Park.
2. Chicago Jazz Festival
Produced by DCASE and the Jazz Institute of Chicago, the Chicago Jazz Festival highlights the city’s rich jazz heritage with performances from both local legends and international stars. Concerts are held at Millennium Park and the Chicago Cultural Center.
- When/Where: Aug. 28–31, various times, Downtown Chicago.
3. North Coast Music Festival
The North Coast Music Festival returns for its 15th year with a massive lineup of electronic music stars. Expect immersive stage production, high-energy performances, and late-night vibes at SeatGeek Stadium in Bridgeview.
- When/Where: Aug. 29–31, 2 p.m.–12 a.m.
4. ARC Music Festival
Chicago’s own ARC Festival celebrates the birthplace of house music. Held in Union Park, the event brings together top names in house and techno for a weekend of nonstop beats.
- When/Where: Aug. 29–31, Union Park, Chicago.
5. Taste of Polonia
Celebrate Polish culture at the Taste of Polonia Festival with traditional food, live music, beer gardens, and family-friendly entertainment. Hosted at the Copernicus Center, it’s a community favorite for the holiday weekend.
- When/Where: Aug. 29–31, Copernicus Center, 5216 W. Lawrence Ave.
6. African Festival of the Arts
Now in its 35th year, the African Festival of the Arts transforms Washington Park into a lively celebration of African culture with music, cuisine, art, and performances. It’s recognized as Chicago’s largest showcase of global Black culture.
- When/Where: Aug. 30–Sept. 1, 10 a.m.–10 p.m.
7. Bristol Renaissance Faire Closing Weekend
Step back in time at the Bristol Renaissance Faire, just north of the city in Kenosha, Wisconsin. The Labor Day holiday marks the final chance of the year to experience jousts, period costumes, artisan markets, and live entertainment.
- When/Where: Closes Sept. 1, 12550 120th Ave., Kenosha, WI.
8. LaborFest at Daley Plaza
Honor Chicago’s working-class roots at LaborFest, a Labor Day celebration featuring speeches, music, and community events. Held in the heart of downtown, it’s a meaningful way to close out the holiday.
- When/Where: Monday, Sept. 1, Daley Plaza, 50 W. Washington St.
9. Chicago Cubs at Wrigley Field
Baseball fans can spend Labor Day cheering on the Chicago Cubs as they host the Philadelphia Phillies at historic Wrigley Field. Holiday specials and the classic ballpark atmosphere make this a must for sports lovers.
- When/Where: Monday, Sept. 1, 3:10 p.m.
Chicago’s Labor Day weekend 2025 offers something for everyone — from biking along Lake Shore Drive to dancing at Union Park or savoring Polish food at Copernicus Center. Whether you’re seeking music, culture, or sports, the city is packed with options to celebrate summer’s last big weekend.
Stay connected with ChicagoMusicGuide.com for more guides to Chicago festivals, concerts, and cultural events.